Hydrochloric Acid → (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine

HRID 633417ノート

反応式

HRID 633417 の反応式
[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.Cl>C(Cl)Cl.O1CCOCC1.CCOC(C)=O>[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[C:18]([F:21])([F:19])[F:20])[CH2:6][CH2:5][NH:4][CH2:3]1

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 86704509tert-butyl(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

生成物 1

HCID 86704511(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine収率 95%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of tert-butyl (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate (1.6 g, 1.0 eq, 3.9 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. while stirring. 4N HCl in dioxane (10 mL) was added to the above solution and stirred at 0° C. for 30 minutes and brought to room temperature for 3 hours. The volatiles were removed under vacuum to leave a crude solid. The crude mixture was dissolved in EtOAc (100 mL) and partitioned with 1N aqueous NaOH solution (50 mL). Organic layers were separated and the aqueous layer was washed with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give the desired product in 95% yield.

後処理

  1. stirringstirred at 0° C. for 30 minutes
  2. customThe volatiles were removed under vacuum
  3. customto leave a crude solid
  4. custompartitioned with 1N aqueous NaOH solution (50 mL)
  5. customOrganic layers were separated
  6. washthe aqueous layer was washed with EtOAc (50 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-abafd407bdd4465cb710e6182085bfd4
出典データセット
uspto-grants-2016_04
特許番号
US09321763B2

反応ノート

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